# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b-rac
_database_code_depnum_ccdc_archive 'CCDC 2349919'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 N3 O3, C8 H12 N'
_chemical_formula_sum            'C11 H14 N4 O3'
_chemical_formula_weight         250.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9636(3)
_cell_length_b                   6.64630(10)
_cell_length_c                   11.5269(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.410(2)
_cell_angle_gamma                90
_cell_volume                     1209.84(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3790
_cell_measurement_theta_min      5.5850
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.895
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00  81.00   0.50    0.84    --  108.57 -95.00  90.00   52
  2  ω    -36.00  -9.00   0.50    0.21    --  -46.49  41.00 132.00   54
  3  ω   -100.00 -65.00   0.50    0.84    -- -105.44 125.00 150.00   70
  4  ω   -101.00 -46.00   0.50    0.84    -- -105.44  77.00-180.00  110
  5  ω   -101.00 -75.00   0.50    0.21    --  -46.49 -41.00 -20.00   52
  6  ω   -158.00-133.00   0.50    0.84    -- -105.44 -41.00 -20.00   50
  7  ω    -62.00 -32.00   0.50    0.21    --  -46.49 -41.00 -20.00   60
  8  ω     20.00  46.00   0.50    0.21    --   49.62 -41.00 -20.00   52
  9  ω    -23.00  15.00   0.50    0.21    --   49.62 -41.00 -20.00   76
 10  ω     -9.00  16.00   0.50    0.21    --   49.62 -19.00-150.00   50
 11  ω    -26.00  25.00   0.50    0.21    --   49.62 -19.00-180.00  102
 12  ω     38.00  65.00   0.50    0.84    --  108.57 -61.00 -60.00   54
 13  ω     39.00  64.00   0.50    0.84    --  108.57 -61.00-120.00   50
 14  ω     36.00  71.00   0.50    0.84    --  108.57 -61.00-180.00   70
 15  ω     36.00  71.00   0.50    0.84    --  108.57 -61.00 -30.00   70
 16  ω     43.00  68.00   0.50    0.84    --  108.57 -61.00  30.00   50
 17  ω     36.00  68.00   0.50    0.84    --  108.57 -61.00  60.00   64
 18  ω     37.00  70.00   0.50    0.84    --  108.57 -61.00 120.00   66
 19  ω     36.00  69.00   0.50    0.84    --  108.57 -61.00 150.00   66
 20  ω     38.00  70.00   0.50    0.84    --  108.57 -61.00   0.00   64
 21  ω     38.00  71.00   0.50    0.84    --  108.57 -61.00-150.00   66
 22  ω    125.00 163.00   0.50    0.84    --  108.57  30.00-150.00   76
 23  ω    132.00 172.00   0.50    0.84    --  108.57  45.00  30.00   80
 24  ω     94.00 170.00   0.50    0.84    --  108.57  41.00 132.00  152
 25  ω     39.00 123.00   0.50    0.21    --   49.62  41.00 132.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0882886000
_diffrn_orient_matrix_UB_12      -0.0661972000
_diffrn_orient_matrix_UB_13      -0.0239741000
_diffrn_orient_matrix_UB_21      -0.0403352000
_diffrn_orient_matrix_UB_22      -0.0981584000
_diffrn_orient_matrix_UB_23      -0.1159178000
_diffrn_orient_matrix_UB_31      0.0095542000
_diffrn_orient_matrix_UB_32      0.1992437000
_diffrn_orient_matrix_UB_33      -0.0652362000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2085
_reflns_number_total             2429
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C5(H5), C8(H8), C6(H6), C7(H7)
4.c Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.60973(6) 0.29619(12) 0.46698(7) 0.0391(2) Uani 1 1 d . . . . .
O3 O 0.67257(7) 0.86928(13) 0.67364(8) 0.0438(3) Uani 1 1 d . . . . .
N3 N 0.64102(6) 0.57320(14) 0.57953(8) 0.0307(2) Uani 1 1 d . . . . .
N2 N 0.56012(7) 0.59262(14) 0.39200(8) 0.0318(2) Uani 1 1 d . . . . .
H2 H 0.536308 0.530128 0.330573 0.038 Uiso 1 1 calc R U . . .
O1 O 0.51242(8) 0.89303(15) 0.31593(8) 0.0530(3) Uani 1 1 d . . . . .
N1 N 0.59126(7) 0.88130(14) 0.49618(8) 0.0317(2) Uani 1 1 d . . . . .
H1 H 0.587761 1.009739 0.503144 0.038 Uiso 1 1 calc R U . . .
N4 N 0.68030(6) 0.27261(15) 0.75226(8) 0.0332(2) Uani 1 1 d . . . . .
H4A H 0.670103 0.372255 0.700538 0.040 Uiso 1 1 calc R U . . .
H4B H 0.643441 0.278731 0.803097 0.040 Uiso 1 1 calc R U . . .
H4C H 0.674966 0.155118 0.714867 0.040 Uiso 1 1 calc R U . . .
C2 C 0.60464(7) 0.48095(17) 0.48152(9) 0.0273(2) Uani 1 1 d . . . . .
C3 C 0.63674(7) 0.77510(18) 0.58827(10) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.55190(8) 0.79562(17) 0.39570(10) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.76846(8) 0.2924(2) 0.81667(11) 0.0389(3) Uani 1 1 d . . . . .
H10 H 0.777411 0.183856 0.874722 0.047 Uiso 1 1 calc R U . . .
C4 C 0.83258(9) 0.2669(2) 0.73333(11) 0.0432(3) Uani 1 1 d . . . . .
C11 C 0.77608(10) 0.4913(3) 0.88241(14) 0.0556(4) Uani 1 1 d . . . . .
H11A H 0.758278 0.598913 0.828909 0.083 Uiso 1 1 calc R U . . .
H11B H 0.833924 0.512175 0.916722 0.083 Uiso 1 1 calc R U . . .
H11C H 0.740847 0.488374 0.943123 0.083 Uiso 1 1 calc R U . . .
C9 C 0.84683(10) 0.4175(3) 0.65506(14) 0.0569(4) Uani 1 1 d . . . . .
H9 H 0.815193 0.535444 0.651077 0.068 Uiso 1 1 calc R U . . .
C5 C 0.88061(11) 0.0924(3) 0.73669(15) 0.0587(4) Uani 1 1 d . . . . .
H5 H 0.871029 -0.010807 0.787601 0.070 Uiso 1 1 calc R U . . .
C8 C 0.90860(13) 0.3918(4) 0.58246(16) 0.0733(6) Uani 1 1 d . U . . .
H8 H 0.917482 0.491864 0.529203 0.088 Uiso 1 1 calc R U . . .
C6 C 0.94273(13) 0.0699(4) 0.66519(18) 0.0746(6) Uani 1 1 d . . . . .
H6 H 0.974951 -0.047167 0.669191 0.090 Uiso 1 1 calc R U . . .
C7 C 0.95657(12) 0.2185(4) 0.58929(17) 0.0769(6) Uani 1 1 d . U . . .
H7 H 0.998513 0.203365 0.541827 0.092 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.2436(15) . ?
O3 C3 1.2339(14) . ?
N3 C2 1.3407(15) . ?
N3 C3 1.3482(16) . ?
N2 H2 0.8600 . ?
N2 C2 1.3807(14) . ?
N2 C1 1.3569(15) . ?
O1 C1 1.2216(15) . ?
N1 H1 0.8600 . ?
N1 C3 1.3881(14) . ?
N1 C1 1.3592(15) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N4 C10 1.4978(16) . ?
C10 H10 0.9800 . ?
C10 C4 1.5123(19) . ?
C10 C11 1.520(2) . ?
C4 C9 1.389(2) . ?
C4 C5 1.387(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.394(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.359(3) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 C3 119.85(9) . . ?
C2 N2 H2 118.2 . . ?
C1 N2 H2 118.2 . . ?
C1 N2 C2 123.54(10) . . ?
C3 N1 H1 117.9 . . ?
C1 N1 H1 117.9 . . ?
C1 N1 C3 124.30(10) . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C10 N4 H4A 109.5 . . ?
C10 N4 H4B 109.5 . . ?
C10 N4 H4C 109.5 . . ?
O2 C2 N3 122.44(10) . . ?
O2 C2 N2 117.82(10) . . ?
N3 C2 N2 119.74(10) . . ?
O3 C3 N3 122.81(10) . . ?
O3 C3 N1 118.79(11) . . ?
N3 C3 N1 118.39(10) . . ?
N2 C1 N1 114.12(10) . . ?
O1 C1 N2 123.02(11) . . ?
O1 C1 N1 122.86(11) . . ?
N4 C10 H10 107.9 . . ?
N4 C10 C4 110.46(10) . . ?
N4 C10 C11 108.92(11) . . ?
C4 C10 H10 107.9 . . ?
C4 C10 C11 113.70(12) . . ?
C11 C10 H10 107.9 . . ?
C9 C4 C10 121.49(14) . . ?
C5 C4 C10 119.91(14) . . ?
C5 C4 C9 118.57(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C9 H9 120.0 . . ?
C4 C9 C8 119.94(18) . . ?
C8 C9 H9 120.0 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(18) . . ?
C6 C5 H5 119.5 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.26(19) . . ?
C7 C8 H8 119.9 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.10(19) . . ?
C7 C6 H6 119.9 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.18(18) . . ?
C6 C7 H7 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.86 1.98 2.8343(13) 176.3 2_645 yes
N1 H1 O2 0.86 1.99 2.7988(13) 156.0 1_565 yes
N4 H4A N3 0.89 1.94 2.8254(14) 174.9 . yes
N4 H4C O3 0.89 1.96 2.8266(14) 165.1 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C10 C4 C9 74.75(16) . . . . ?
N4 C10 C4 C5 -107.31(15) . . . . ?
C2 N3 C3 O3 -176.21(11) . . . . ?
C2 N3 C3 N1 2.62(17) . . . . ?
C2 N2 C1 O1 179.92(12) . . . . ?
C2 N2 C1 N1 -0.26(18) . . . . ?
C3 N3 C2 O2 176.93(11) . . . . ?
C3 N3 C2 N2 -2.59(17) . . . . ?
C3 N1 C1 N2 0.33(17) . . . . ?
C3 N1 C1 O1 -179.85(13) . . . . ?
C1 N2 C2 O2 -178.13(11) . . . . ?
C1 N2 C2 N3 1.40(18) . . . . ?
C1 N1 C3 O3 177.35(12) . . . . ?
C1 N1 C3 N3 -1.53(18) . . . . ?
C10 C4 C9 C8 177.68(14) . . . . ?
C10 C4 C5 C6 -176.77(15) . . . . ?
C4 C9 C8 C7 -1.0(3) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C11 C10 C4 C9 -48.05(18) . . . . ?
C11 C10 C4 C5 129.88(15) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C9 C8 C7 C6 1.4(3) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.195
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c-s
_database_code_depnum_ccdc_archive 'CCDC 2349920'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        S-a-MBACY
_chemical_formula_moiety         'C3 H2 N3 O3, C8 H12 N'
_chemical_formula_sum            'C11 H14 N4 O3'
_chemical_formula_weight         250.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H14 N4 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.84020(10)
_cell_length_b                   12.41110(10)
_cell_length_c                   12.47300(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.7460(10)
_cell_angle_gamma                90
_cell_volume                     1205.29(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      3.5360
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.608
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44159
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.526
_diffrn_reflns_theta_min         3.568
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -13.00   0.50    0.05    --  -47.74 125.00 150.00  162
  2  ω   -108.00 -48.00   0.50    0.45    -- -105.00 125.00 -30.00  120
  3  ω    -73.00 -37.00   0.50    0.45    -- -105.00 125.00 -90.00   72
  4  ω   -111.00 -83.00   0.50    0.45    -- -105.00 125.00 -90.00   56
  5  ω    -25.00  27.00   0.50    0.05    --  -47.74   9.00 -33.00  104
  6  ω     24.00 121.00   0.50    0.05    --   47.74  77.00-120.00  194
  7  ω     32.00 121.00   0.50    0.05    --   47.74  57.00 -90.00  178
  8  ω     20.00 123.00   0.50    0.05    --   47.74   9.00 -33.00  206
  9  ω     32.00 121.00   0.50    0.05    --   47.74  57.00   0.00  178
 10  ω     32.00 121.00   0.50    0.05    --   47.74  57.00  60.00  178
 11  ω     85.00 173.00   0.50    0.45    --  108.08  77.00 -30.00  176
 12  ω     80.00 176.00   0.50    0.45    --  108.08   9.00 -33.00  192
 13  ω    -26.00  43.00   0.50    0.05    --   47.74 -38.00   0.00  138
 14  ω    -27.00  25.00   0.50    0.05    --   47.74  -9.00 152.00  104
 15  ω     36.00 104.00   0.50    0.45    --  108.08 -77.00  30.00  136
 16  ω     69.00 103.00   0.50    0.45    --  108.08 -77.00 120.00   68
 17  ω     41.00  66.00   0.50    0.45    --  108.08 -77.00 120.00   50
 18  ω     37.00  95.00   0.50    0.45    --  108.08 -77.00  90.00  116
 19  ω     60.00 101.00   0.50    0.45    --  108.08 -95.00 120.00   82
 20  ω     39.00  64.00   0.50    0.45    --  108.08-125.00  90.00   50
 21  ω     73.00 111.00   0.50    0.45    --  108.08-125.00  90.00   76
 22  ω     13.00  94.00   0.50    0.05    --   47.74-125.00  60.00  162
 23  ω     39.00  64.00   0.50    0.45    --  108.08-125.00 -30.00   50
 24  ω     36.00  93.00   0.50    0.45    --  108.08 -95.00   0.00  114
 25  ω     77.00 112.00   0.50    0.45    --  108.08-125.00 -30.00   70
 26  ω     35.00 105.00   0.50    0.45    --  108.08 -95.00 -90.00  140
 27  ω     63.00 112.00   0.50    0.45    --  108.08-125.00-120.00   98
 28  ω     39.00  93.00   0.50    0.45    --  108.08-125.00 -90.00  108
 29  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  90.00  192
 30  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 120.00  192
 31  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 150.00  192
 32  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  90.00  192
 33  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  30.00  192
 34  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 -30.00  192
 35  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 -60.00  192
 36  ω   -120.00 -31.00   0.50    0.05    --  -47.74 -57.00 -90.00  178
 37  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00-120.00  192
 38  ω   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00-180.00  192
 39  ω   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 -90.00  176
 40  ω   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 -90.00  176
 41  ω   -120.00 -32.00   0.50    0.05    --  -47.74 -46.00 110.08  176
 42  ω   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 120.00  176
 43  ω   -123.00 -23.00   0.50    0.05    --  -47.74  -9.00 152.00  200
 44  ω   -123.00 -23.00   0.50    0.05    --  -47.74  -9.00 152.00  200
 45  ω   -175.00-137.00   0.50    0.45    -- -105.00 -77.00  53.55   76
 46  ω   -169.00-143.00   0.50    0.45    -- -105.00 -77.00 150.00   52
 47  ω   -107.00 -81.00   0.50    0.45    -- -105.00 -77.00  53.55   52
 48  ω   -109.00 -81.00   0.50    0.45    -- -105.00 -77.00 150.00   56
 49  ω   -110.00 -81.00   0.50    0.45    -- -105.00 -77.00   0.00   58
 50  ω   -109.00 -82.00   0.50    0.45    -- -105.00 -77.00 -30.00   54
 51  ω   -174.00 -81.00   0.50    0.45    -- -105.00 -76.00 -51.49  186
 52  ω   -172.00-146.00   0.50    0.45    -- -105.00 -77.00   0.00   52
 53  ω   -109.00 -82.00   0.50    0.45    -- -105.00 -75.00  10.57   54
 54  ω   -108.00 -82.00   0.50    0.45    -- -105.00 -75.00 -38.00   52
 55  ω   -108.00 -82.00   0.50    0.45    -- -105.00 -75.00 -44.53   52
 56  ω   -113.00 -86.00   0.50    0.45    -- -105.00 -77.00-150.00   54
 57  ω   -175.00-116.00   0.50    0.45    -- -105.00 -77.00-150.00  118
 58  ω   -145.00-120.00   0.50    0.45    -- -105.00 -75.00 -38.00   50
 59  ω   -173.00-121.00   0.50    0.45    -- -105.00 -75.00  10.57  104
 60  ω   -164.00-137.00   0.50    0.45    -- -105.00 -71.00 -64.94   54
 61  ω   -117.00 -84.00   0.50    0.45    -- -105.00 -71.00 -64.94   66
 62  ω   -111.00 -85.00   0.50    0.45    -- -105.00 -68.00 112.31   52
 63  ω   -109.00 -83.00   0.50    0.45    -- -105.00 -72.00 151.01   52
 64  ω   -118.00 -85.00   0.50    0.45    -- -105.00 -67.00 124.74   66
 65  ω   -109.00 -83.00   0.50    0.45    -- -105.00 -72.00 175.53   52
 66  ω   -111.00 -85.00   0.50    0.45    -- -105.00 -68.00 177.49   52
 67  ω   -170.00 -86.00   0.50    0.45    -- -105.00 -64.00 152.40  168
 68  ω   -168.00-119.00   0.50    0.45    -- -105.00 -72.00 175.53   98
 69  ω   -173.00-148.00   0.50    0.45    -- -105.00 -68.00 112.31   50
 70  ω   -170.00 -86.00   0.50    0.45    -- -105.00 -64.00 115.66  168
 71  ω   -122.00 -86.00   0.50    0.45    -- -105.00 -64.00 100.06   72
 72  ω   -124.00 -86.00   0.50    0.45    -- -105.00 -64.00  16.76   76
 73  ω   -171.00-145.00   0.50    0.45    -- -105.00 -64.00  16.76   52
 74  ω   -170.00-145.00   0.50    0.45    -- -105.00 -63.00 -83.03   50
 75  ω   -121.00 -87.00   0.50    0.45    -- -105.00 -63.00 -91.37   68
 76  ω   -113.00 -88.00   0.50    0.45    -- -105.00 -63.00 -83.03   50
 77  ω   -170.00 -87.00   0.50    0.45    -- -105.00 -63.00-140.64  166
 78  ω   -163.00 -86.00   0.50    0.45    -- -105.00 -65.00-130.33  154
 79  ω   -125.00 -87.00   0.50    0.45    -- -105.00 -61.00   0.00   76
 80  ω   -172.00 -87.00   0.50    0.45    -- -105.00 -61.00 -30.00  170
 81  ω   -120.00 -88.00   0.50    0.45    -- -105.00 -62.00  86.87   64
 82  ω   -112.00 -87.00   0.50    0.45    -- -105.00 -61.00  90.00   50
 83  ω   -152.00 -87.00   0.50    0.45    -- -105.00 -62.00  77.23  130
 84  ω   -175.00-134.00   0.50    0.45    -- -105.00 -61.00  90.00   82
 85  ω   -128.00 -90.00   0.50    0.45    -- -105.00 -61.00-120.00   76
 86  ω   -131.00 -89.00   0.50    0.45    -- -105.00 -60.00-128.17   84
 87  ω   -113.00 -88.00   0.50    0.45    -- -105.00 -59.00-115.62   50
 88  ω   -118.00 -89.00   0.50    0.45    -- -105.00 -55.00-161.40   58
 89  ω   -152.00-126.00   0.50    0.45    -- -105.00 -59.00-115.62   52
 90  ω   -170.00 -89.00   0.50    0.45    -- -105.00 -56.00-110.85  162
 91  ω   -117.00 -88.00   0.50    0.45    -- -105.00 -59.00  21.37   58
 92  ω   -128.00 -88.00   0.50    0.45    -- -105.00 -54.00  34.23   80
 93  ω   -116.00 -88.00   0.50    0.45    -- -105.00 -54.00  56.39   56
 94  ω   -124.00 -88.00   0.50    0.45    -- -105.00 -54.00  45.02   72
 95  ω   -174.00 -90.00   0.50    0.45    -- -105.00 -54.00 134.99  168
 96  ω   -171.00-142.00   0.50    0.45    -- -105.00 -45.00 174.23   58
 97  ω   -121.00 -90.00   0.50    0.45    -- -105.00 -45.00 174.23   62
 98  ω   -126.00 -90.00   0.50    0.45    -- -105.00 -44.00 164.31   72
 99  ω   -175.00 -81.00   0.50    0.45    -- -105.00  -9.00 152.00  188
100  ω   -165.00-139.00   0.50    0.45    -- -105.00 -54.00  56.39   52
101  ω   -115.00 -89.00   0.50    0.45    -- -105.00 -51.00 -57.00   52
102  ω   -126.00 -90.00   0.50    0.45    -- -105.00 -45.00 -60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1020791000
_diffrn_orient_matrix_UB_12      -0.0079272000
_diffrn_orient_matrix_UB_13      0.1130498000
_diffrn_orient_matrix_UB_21      -0.1691094000
_diffrn_orient_matrix_UB_22      -0.0135707000
_diffrn_orient_matrix_UB_23      0.0502428000
_diffrn_orient_matrix_UB_31      0.0120622000
_diffrn_orient_matrix_UB_32      -0.1230998000
_diffrn_orient_matrix_UB_33      -0.0128655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                4596
_reflns_number_total             4730
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2), N1(H1), N4(H4), C12(H12), C10(H10), C9(H9), C8(H8), C16(H16),
 C11(H11), C20(H20), C17(H17), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 N8(H8A,H8B,H8C), N7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 1.1046(2) 0.40313(12) 0.69095(11) 0.0476(4) Uani 1 1 d . . . . .
O2 O 1.53241(18) 0.58106(13) 0.16843(10) 0.0428(3) Uani 1 1 d . . . . .
O3 O 1.3668(2) 0.30212(12) -0.05421(12) 0.0521(4) Uani 1 1 d . . . . .
O6 O 1.1258(2) 0.74766(13) 0.57872(12) 0.0533(4) Uani 1 1 d . . . . .
O5 O 0.8353(2) 0.49960(15) 0.36278(12) 0.0585(5) Uani 1 1 d . . . . .
N5 N 0.9702(2) 0.44894(14) 0.52461(12) 0.0390(4) Uani 1 1 d . . . . .
H5 H 0.938684 0.383578 0.510570 0.047 Uiso 1 1 calc R U . . .
O1 O 1.3388(3) 0.64208(14) -0.18249(13) 0.0631(5) Uani 1 1 d . . . . .
N2 N 1.4458(2) 0.61176(14) -0.00754(13) 0.0401(4) Uani 1 1 d . . . . .
H2 H 1.473697 0.678438 0.001466 0.048 Uiso 1 1 calc R U . . .
N8 N 0.8382(2) 0.68675(14) 0.23210(12) 0.0350(3) Uani 1 1 d . . . . .
H8A H 0.737298 0.698488 0.193184 0.042 Uiso 1 1 calc R U . . .
H8B H 0.862241 0.741173 0.277844 0.042 Uiso 1 1 calc R U . . .
H8C H 0.833451 0.625669 0.269019 0.042 Uiso 1 1 calc R U . . .
N3 N 1.4510(2) 0.43584(15) 0.06533(12) 0.0384(4) Uani 1 1 d . . . . .
N1 N 1.3376(2) 0.47297(14) -0.11401(12) 0.0414(4) Uani 1 1 d . . . . .
H1 H 1.282023 0.449536 -0.172948 0.050 Uiso 1 1 calc R U . . .
N4 N 1.1084(2) 0.57668(14) 0.63433(13) 0.0427(4) Uani 1 1 d . . . . .
H4 H 1.164617 0.595357 0.694834 0.051 Uiso 1 1 calc R U . . .
N7 N 1.5765(2) 0.35517(15) 0.27608(12) 0.0406(4) Uani 1 1 d . . . . .
H7A H 1.559224 0.373478 0.206667 0.049 Uiso 1 1 calc R U . . .
H7B H 1.604037 0.285669 0.281812 0.049 Uiso 1 1 calc R U . . .
H7C H 1.661677 0.394564 0.309347 0.049 Uiso 1 1 calc R U . . .
N6 N 0.9713(2) 0.63062(15) 0.46515(14) 0.0456(4) Uani 1 1 d . . . . .
C2 C 1.4784(2) 0.54191(17) 0.08008(14) 0.0347(4) Uani 1 1 d . . . . .
C4 C 1.0643(2) 0.47116(16) 0.62096(14) 0.0358(4) Uani 1 1 d . . . . .
C3 C 1.3868(2) 0.39847(16) -0.03188(14) 0.0372(4) Uani 1 1 d . . . . .
C6 C 1.0689(3) 0.65685(16) 0.55699(15) 0.0390(4) Uani 1 1 d . . . . .
C1 C 1.3723(3) 0.57975(17) -0.10611(15) 0.0411(4) Uani 1 1 d . . . . .
C7 C 1.4503(3) 0.3618(2) 0.44850(16) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.9233(3) 0.52854(18) 0.44812(15) 0.0414(4) Uani 1 1 d . . . . .
C13 C 1.4156(3) 0.3750(2) 0.32736(16) 0.0479(5) Uani 1 1 d . . . . .
H13 H 1.381188 0.450001 0.312666 0.057 Uiso 1 1 calc R U . . .
C15 C 0.9298(3) 0.5930(2) 0.07432(19) 0.0523(5) Uani 1 1 d . . . . .
C21 C 0.9740(3) 0.6783(2) 0.15923(18) 0.0483(5) Uani 1 1 d . . . . .
H21 H 0.980693 0.747620 0.122363 0.058 Uiso 1 1 calc R U . . .
C12 C 1.4849(5) 0.4506(3) 0.5128(2) 0.0696(7) Uani 1 1 d . . . . .
H12 H 1.485062 0.518816 0.481869 0.083 Uiso 1 1 calc R U . . .
C10 C 1.5169(3) 0.3399(3) 0.67098(19) 0.0683(8) Uani 1 1 d . . . . .
H10 H 1.539892 0.332766 0.745499 0.082 Uiso 1 1 calc R U . . .
C9 C 1.4808(4) 0.2521(3) 0.6087(2) 0.0657(7) Uani 1 1 d . . . . .
H9 H 1.478717 0.184387 0.640380 0.079 Uiso 1 1 calc R U . . .
C8 C 1.4468(4) 0.2626(2) 0.4978(2) 0.0594(6) Uani 1 1 d . . . . .
H8 H 1.421120 0.201495 0.455791 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9058(4) 0.4866(3) 0.1000(3) 0.0675(7) Uani 1 1 d . . . . .
H16 H 0.919077 0.464986 0.171908 0.081 Uiso 1 1 calc R U . . .
C11 C 1.5197(5) 0.4389(3) 0.6245(2) 0.0838(10) Uani 1 1 d . . . . .
H11 H 1.544947 0.499341 0.667503 0.101 Uiso 1 1 calc R U . . .
C14 C 1.2742(4) 0.3034(4) 0.2737(2) 0.0888(12) Uani 1 1 d . . . . .
H14A H 1.255125 0.319535 0.197939 0.133 Uiso 1 1 calc R U . . .
H14B H 1.170390 0.315901 0.305639 0.133 Uiso 1 1 calc R U . . .
H14C H 1.307376 0.229228 0.283395 0.133 Uiso 1 1 calc R U . . .
C22 C 1.1441(3) 0.6595(3) 0.2278(3) 0.0770(9) Uani 1 1 d . . . . .
H22A H 1.162407 0.714897 0.281590 0.115 Uiso 1 1 calc R U . . .
H22B H 1.235330 0.661177 0.182727 0.115 Uiso 1 1 calc R U . . .
H22C H 1.142445 0.590476 0.262389 0.115 Uiso 1 1 calc R U . . .
C20 C 0.9106(4) 0.6227(3) -0.0343(2) 0.0744(9) Uani 1 1 d . . . . .
H20 H 0.924597 0.694368 -0.053078 0.089 Uiso 1 1 calc R U . . .
C17 C 0.8615(5) 0.4109(3) 0.0183(4) 0.0927(12) Uani 1 1 d . . . . .
H17 H 0.842557 0.339358 0.035790 0.111 Uiso 1 1 calc R U . . .
C19 C 0.8710(5) 0.5468(5) -0.1139(3) 0.0990(15) Uani 1 1 d . . . . .
H19 H 0.861441 0.567398 -0.186045 0.119 Uiso 1 1 calc R U . . .
C18 C 0.8459(5) 0.4428(4) -0.0883(3) 0.0992(15) Uani 1 1 d . . . . .
H18 H 0.818100 0.392455 -0.142803 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.229(2) . ?
O2 C2 1.233(2) . ?
O3 C3 1.234(3) . ?
O6 C6 1.231(3) . ?
O5 C5 1.251(2) . ?
N5 H5 0.8600 . ?
N5 C4 1.362(2) . ?
N5 C5 1.392(2) . ?
O1 C1 1.231(2) . ?
N2 H2 0.8600 . ?
N2 C2 1.395(2) . ?
N2 C1 1.355(2) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N8 C21 1.483(3) . ?
N3 C2 1.343(3) . ?
N3 C3 1.340(2) . ?
N1 H1 0.8600 . ?
N1 C3 1.400(2) . ?
N1 C1 1.354(3) . ?
N4 H4 0.8600 . ?
N4 C4 1.360(3) . ?
N4 C6 1.395(3) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
N7 C13 1.500(3) . ?
N6 C6 1.341(2) . ?
N6 C5 1.331(3) . ?
C7 C13 1.513(3) . ?
C7 C12 1.371(4) . ?
C7 C8 1.378(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.515(4) . ?
C15 C21 1.509(3) . ?
C15 C16 1.376(5) . ?
C15 C20 1.395(4) . ?
C21 H21 0.9800 . ?
C21 C22 1.516(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.395(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.349(5) . ?
C10 C11 1.360(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(3) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.400(4) . ?
C11 H11 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.378(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.349(8) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 H5 118.9 . . ?
C4 N5 C5 122.19(17) . . ?
C5 N5 H5 118.9 . . ?
C2 N2 H2 118.4 . . ?
C1 N2 H2 118.4 . . ?
C1 N2 C2 123.24(17) . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
C21 N8 H8A 109.5 . . ?
C21 N8 H8B 109.5 . . ?
C21 N8 H8C 109.5 . . ?
C3 N3 C2 120.02(16) . . ?
C3 N1 H1 118.1 . . ?
C1 N1 H1 118.1 . . ?
C1 N1 C3 123.87(16) . . ?
C4 N4 H4 117.6 . . ?
C4 N4 C6 124.72(16) . . ?
C6 N4 H4 117.6 . . ?
H7A N7 H7B 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
C13 N7 H7A 109.5 . . ?
C13 N7 H7B 109.5 . . ?
C13 N7 H7C 109.5 . . ?
C5 N6 C6 119.30(17) . . ?
O2 C2 N2 117.87(18) . . ?
O2 C2 N3 122.78(17) . . ?
N3 C2 N2 119.35(16) . . ?
O4 C4 N5 123.71(18) . . ?
O4 C4 N4 122.30(16) . . ?
N4 C4 N5 113.99(16) . . ?
O3 C3 N3 124.34(17) . . ?
O3 C3 N1 117.27(17) . . ?
N3 C3 N1 118.39(18) . . ?
O6 C6 N4 117.11(17) . . ?
O6 C6 N6 124.49(18) . . ?
N6 C6 N4 118.40(18) . . ?
O1 C1 N2 123.18(19) . . ?
O1 C1 N1 122.39(17) . . ?
N1 C1 N2 114.42(17) . . ?
C12 C7 C13 119.8(2) . . ?
C12 C7 C8 118.1(2) . . ?
C8 C7 C13 122.2(2) . . ?
O5 C5 N5 117.00(19) . . ?
O5 C5 N6 121.74(18) . . ?
N6 C5 N5 121.26(16) . . ?
N7 C13 C7 110.27(16) . . ?
N7 C13 H13 107.7 . . ?
N7 C13 C14 108.9(2) . . ?
C7 C13 H13 107.7 . . ?
C7 C13 C14 114.5(2) . . ?
C14 C13 H13 107.7 . . ?
C16 C15 C21 122.4(2) . . ?
C16 C15 C20 118.5(3) . . ?
C20 C15 C21 119.1(3) . . ?
N8 C21 C15 110.96(18) . . ?
N8 C21 H21 107.9 . . ?
N8 C21 C22 108.2(2) . . ?
C15 C21 H21 107.9 . . ?
C15 C21 C22 113.7(2) . . ?
C22 C21 H21 107.9 . . ?
C7 C12 H12 119.9 . . ?
C7 C12 C11 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 H17 120.2 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O6 0.86 2.05 2.871(2) 158.9 2_746 yes
N2 H2 O3 0.86 2.04 2.840(2) 154.6 2_855 yes
N8 H8A O2 0.89 2.16 2.766(2) 124.4 1_455 yes
N8 H8B O4 0.89 2.06 2.869(2) 151.0 2_756 yes
N8 H8C O5 0.89 1.95 2.839(2) 174.1 . yes
N4 H4 O1 0.86 2.01 2.859(2) 167.7 1_556 yes
N7 H7A N3 0.89 2.02 2.876(2) 161.4 . yes
N7 H7C O5 0.89 1.95 2.826(2) 169.9 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 O1 177.7(2) . . . . ?
C2 N2 C1 N1 -2.0(3) . . . . ?
C2 N3 C3 O3 175.7(2) . . . . ?
C2 N3 C3 N1 -4.8(3) . . . . ?
C4 N5 C5 O5 -179.3(2) . . . . ?
C4 N5 C5 N6 1.1(3) . . . . ?
C4 N4 C6 O6 -176.1(2) . . . . ?
C4 N4 C6 N6 4.5(3) . . . . ?
C3 N3 C2 O2 177.78(17) . . . . ?
C3 N3 C2 N2 -2.5(3) . . . . ?
C3 N1 C1 O1 174.4(2) . . . . ?
C3 N1 C1 N2 -5.8(3) . . . . ?
C6 N4 C4 O4 178.8(2) . . . . ?
C6 N4 C4 N5 -2.3(3) . . . . ?
C6 N6 C5 O5 -178.5(2) . . . . ?
C6 N6 C5 N5 1.1(3) . . . . ?
C1 N2 C2 O2 -174.01(18) . . . . ?
C1 N2 C2 N3 6.3(3) . . . . ?
C1 N1 C3 O3 -170.9(2) . . . . ?
C1 N1 C3 N3 9.5(3) . . . . ?
C7 C12 C11 C10 -1.1(6) . . . . ?
C5 N5 C4 O4 178.42(19) . . . . ?
C5 N5 C4 N4 -0.5(3) . . . . ?
C5 N6 C6 O6 176.9(2) . . . . ?
C5 N6 C6 N4 -3.6(3) . . . . ?
C13 C7 C12 C11 -179.0(3) . . . . ?
C13 C7 C8 C9 179.3(2) . . . . ?
C15 C16 C17 C18 1.6(5) . . . . ?
C15 C20 C19 C18 1.6(5) . . . . ?
C21 C15 C16 C17 178.7(2) . . . . ?
C21 C15 C20 C19 179.7(3) . . . . ?
C12 C7 C13 N7 96.4(3) . . . . ?
C12 C7 C13 C14 -140.4(3) . . . . ?
C12 C7 C8 C9 -1.4(4) . . . . ?
C10 C9 C8 C7 0.5(4) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C8 C7 C13 N7 -84.3(3) . . . . ?
C8 C7 C13 C14 38.9(4) . . . . ?
C8 C7 C12 C11 1.7(5) . . . . ?
C16 C15 C21 N8 -60.0(3) . . . . ?
C16 C15 C21 C22 62.3(3) . . . . ?
C16 C15 C20 C19 -1.0(4) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C11 C10 C9 C8 0.1(4) . . . . ?
C20 C15 C21 N8 119.3(2) . . . . ?
C20 C15 C21 C22 -118.4(3) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?
C20 C19 C18 C17 -0.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 2349921'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 N3 O3, C8 H12 N'
_chemical_formula_sum            'C11 H14 N4 O3'
_chemical_formula_weight         250.26
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.84010(10)
_cell_length_b                   12.40940(10)
_cell_length_c                   12.46850(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.7100(10)
_cell_angle_gamma                90
_cell_volume                     1204.76(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.5310
_cell_measurement_theta_min      3.5160
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32451
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.841
_diffrn_reflns_theta_min         3.569
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 120.00   0.50    0.06    --   46.74  77.00 120.00  194
  2  ω     23.00 120.00   0.50    0.06    --   46.74  77.00   0.00  194
  3  ω     31.00 120.00   0.50    0.06    --   46.74  57.00 -30.00  178
  4  ω     31.00 120.00   0.50    0.06    --   46.74  57.00  90.00  178
  5  ω     23.00 120.00   0.50    0.06    --   46.74  77.00-120.00  194
  6  ω     31.00 120.00   0.50    0.06    --   46.74  57.00-150.00  178
  7  ω     99.00 176.00   0.50    0.25    --  113.25  45.00 -90.00  154
  8  ω     99.00 176.00   0.50    0.25    --  113.25  45.00 -60.00  154
  9  ω     99.00 176.00   0.50    0.25    --  113.25  30.00-150.00  154
 10  ω     99.00 176.00   0.50    0.25    --  113.25  30.00-150.00  154
 11  ω     96.00 176.00   0.50    0.25    --  113.25  15.00-120.00  160
 12  ω     41.00 106.00   0.50    0.25    --  113.25 -95.00-180.00  130
 13  ω     41.00 106.00   0.50    0.25    --  113.25 -95.00 -90.00  130
 14  ω     43.00 111.00   0.50    0.25    --  113.25-125.00 -90.00  136
 15  ω     41.00 106.00   0.50    0.25    --  113.25 -95.00 -30.00  130
 16  ω     41.00 106.00   0.50    0.25    --  113.25 -95.00  90.00  130
 17  ω     41.00 105.00   0.50    0.25    --  113.25 -77.00 150.00  128
 18  ω     41.00 105.00   0.50    0.25    --  113.25 -77.00 150.00  128
 19  ω    -27.00  43.00   0.50    0.06    --   46.74 -38.00 120.00  140
 20  ω    -29.00  26.00   0.50    0.06    --   46.74 -19.00  30.00  110
 21  ω     41.00  71.00   0.50    0.25    --  113.25 -61.00-180.00   60
 22  ω    -27.00  43.00   0.50    0.06    --   46.74 -38.00-120.00  140
 23  ω   -119.00 -23.00   0.50    0.06    --  -46.74 -77.00 -90.00  192
 24  ω   -119.00 -46.00   0.50    0.06    --  -46.74 -77.00  30.00  146
 25  ω   -175.00 -87.00   0.50    0.25    -- -105.00 -15.00   0.00  176
 26  ω   -175.00 -81.00   0.50    0.25    -- -105.00 -77.00  30.00  188
 27  ω   -175.00 -90.00   0.50    0.25    -- -105.00 -52.00 104.48  170
 28  ω   -122.00 -31.00   0.50    0.06    --  -46.74 -19.00 120.00  182
 29  ω    -43.00  27.00   0.50    0.06    --  -46.74  38.00 120.00  140
 30  ω    -71.00 -32.00   0.50    0.25    -- -105.00  61.00 150.00   78
 31  ω   -105.00 -32.00   0.50    0.25    -- -105.00  77.00  60.00  146
 32  ω    -71.00 -32.00   0.50    0.25    -- -105.00  61.00  30.00   78
 33  ω    -71.00 -32.00   0.50    0.25    -- -105.00  61.00   0.00   78
 34  ω    -71.00 -32.00   0.50    0.25    -- -105.00  61.00 -90.00   78
 35  ω   -108.00 -35.00   0.50    0.25    -- -105.00 109.00  51.89  146
 36  ω   -112.00 -35.00   0.50    0.25    -- -105.00 125.00 -30.00  154
 37  ω   -132.00 -32.00   0.50    0.25    -- -105.00 155.00  74.82  200
 38  ω   -112.00 -35.00   0.50    0.25    -- -105.00 125.00  60.00  154
 39  ω   -127.00 -32.00   0.50    0.25    -- -105.00 146.00-131.97  190
 40  ω   -127.00 -32.00   0.50    0.25    -- -105.00 146.00-131.97  190
 41  ω    -93.00 -13.00   0.50    0.06    --  -46.74 125.00-150.00  160
 42  ω    113.00 138.00   0.50    0.25    --  113.25  19.00 137.00   50
 43  ω   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00 120.00  192
 44  ω    -26.00  28.00   0.50    0.06    --  -47.73  19.00  30.00  108
 45  ω   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00   0.00  192
 46  ω   -120.00 -31.00   0.50    0.06    --  -47.73 -57.00-180.00  178
 47  ω   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00  90.00  176
 48  ω   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00 -60.00  192
 49  ω   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00 -60.00  176
 50  ω   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00   0.00  176
 51  ω     24.00 120.00   0.50    0.06    --   47.73  77.00  90.00  192
 52  ω    -26.00  43.00   0.50    0.06    --   47.73 -38.00   0.00  138
 53  ω     24.00 120.00   0.50    0.06    --   47.73  77.00-180.00  192
 54  ω   -175.00-128.00   0.50    0.25    -- -105.00 -46.00 154.98   94
 55  ω   -175.00 -90.00   0.50    0.25    -- -105.00 -45.00  60.00  170
 56  ω     96.00 176.00   0.50    0.25    --  113.25  15.00-180.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1790660000
_diffrn_orient_matrix_UB_12      -0.0189314000
_diffrn_orient_matrix_UB_13      -0.0359188000
_diffrn_orient_matrix_UB_21      -0.0834675000
_diffrn_orient_matrix_UB_22      -0.0252269000
_diffrn_orient_matrix_UB_23      -0.1153101000
_diffrn_orient_matrix_UB_31      0.0106951000
_diffrn_orient_matrix_UB_32      0.1200589000
_diffrn_orient_matrix_UB_33      -0.0298925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                4215
_reflns_number_total             4561
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.0770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), N5(H5), N2(H2), C11(H11), C12(H12), C10(H10), C8(H8),
 C20(H20), C9(H9), C16(H16), C19(H19), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 N8(H8A,H8B,H8C), N7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5324(2) 0.41842(16) 0.16826(13) 0.0422(4) Uani 1 1 d . . . . .
O4 O 1.1046(3) 0.59643(15) 0.69095(14) 0.0469(5) Uani 1 1 d . . . . .
O2 O 0.3671(3) 0.69742(15) -0.05418(16) 0.0519(5) Uani 1 1 d . . . . .
O5 O 1.1259(3) 0.25212(16) 0.57877(16) 0.0526(5) Uani 1 1 d . . . . .
N4 N 0.9703(3) 0.55058(17) 0.52491(16) 0.0388(5) Uani 1 1 d . . . . .
H4 H 0.938844 0.615977 0.510958 0.047 Uiso 1 1 calc R U . . .
O6 O 0.8353(3) 0.49995(17) 0.36281(15) 0.0577(6) Uani 1 1 d . . . . .
N1 N 0.4460(3) 0.38787(17) -0.00763(17) 0.0402(5) Uani 1 1 d . . . . .
H1 H 0.473898 0.321180 0.001277 0.048 Uiso 1 1 calc R U . . .
N5 N 1.1084(3) 0.42290(17) 0.63426(17) 0.0425(5) Uani 1 1 d . . . . .
H5 H 1.164686 0.404259 0.694781 0.051 Uiso 1 1 calc R U . . .
O1 O 0.3388(3) 0.35772(17) -0.18250(16) 0.0629(7) Uani 1 1 d . . . . .
N3 N 0.4512(3) 0.56390(18) 0.06537(16) 0.0380(5) Uani 1 1 d . . . . .
N8 N 0.8382(3) 0.31298(17) 0.23216(16) 0.0351(4) Uani 1 1 d . . . . .
H8A H 0.736903 0.303220 0.193119 0.042 Uiso 1 1 calc R U . . .
H8B H 0.835547 0.373276 0.270586 0.042 Uiso 1 1 calc R U . . .
H8C H 0.860642 0.257295 0.276552 0.042 Uiso 1 1 calc R U . . .
N2 N 0.3374(3) 0.52674(17) -0.11390(17) 0.0411(5) Uani 1 1 d . . . . .
H2 H 0.281537 0.550229 -0.172730 0.049 Uiso 1 1 calc R U . . .
N7 N 0.5763(3) 0.64439(18) 0.27616(16) 0.0403(5) Uani 1 1 d . . . . .
H7A H 0.559008 0.625871 0.206779 0.048 Uiso 1 1 calc R U . . .
H7B H 0.661467 0.605062 0.309512 0.048 Uiso 1 1 calc R U . . .
H7C H 0.603877 0.713909 0.281660 0.048 Uiso 1 1 calc R U . . .
N6 N 0.9710(3) 0.36899(19) 0.46538(17) 0.0454(5) Uani 1 1 d . . . . .
C3 C 0.4784(3) 0.4576(2) 0.07994(18) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.3866(3) 0.6013(2) -0.03159(19) 0.0366(5) Uani 1 1 d . . . . .
C4 C 1.0643(3) 0.5285(2) 0.62078(18) 0.0359(5) Uani 1 1 d . . . . .
C5 C 1.0690(3) 0.3428(2) 0.5570(2) 0.0387(6) Uani 1 1 d . . . . .
C1 C 0.3724(4) 0.4202(2) -0.1064(2) 0.0407(6) Uani 1 1 d . . . . .
C7 C 0.4503(4) 0.6380(2) 0.4484(2) 0.0441(6) Uani 1 1 d . . . . .
C6 C 0.9230(4) 0.4711(2) 0.4483(2) 0.0415(6) Uani 1 1 d . . . . .
C13 C 0.4156(4) 0.6248(3) 0.3275(2) 0.0472(6) Uani 1 1 d . . . . .
H13 H 0.380774 0.549858 0.312860 0.057 Uiso 1 1 calc R U . . .
C15 C 0.9294(4) 0.4071(3) 0.0740(2) 0.0518(7) Uani 1 1 d . . . . .
C21 C 0.9739(4) 0.3216(3) 0.1593(2) 0.0480(6) Uani 1 1 d . . . . .
H21 H 0.980747 0.252228 0.122415 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4806(5) 0.7477(3) 0.6086(3) 0.0642(9) Uani 1 1 d . . . . .
H11 H 0.477706 0.815498 0.640190 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4473(5) 0.7370(3) 0.4979(3) 0.0591(8) Uani 1 1 d . . . . .
H12 H 0.422219 0.798106 0.455843 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5174(4) 0.6601(4) 0.6709(2) 0.0672(10) Uani 1 1 d . . . . .
H10 H 0.541038 0.667374 0.745342 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4843(6) 0.5492(3) 0.5129(3) 0.0689(10) Uani 1 1 d . . . . .
H8 H 0.483777 0.481040 0.481891 0.083 Uiso 1 1 calc R U . . .
C20 C 0.9061(5) 0.5130(3) 0.1002(3) 0.0666(9) Uani 1 1 d . . . . .
H20 H 0.919681 0.534394 0.172149 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5197(6) 0.5604(4) 0.6244(3) 0.0841(13) Uani 1 1 d . . . . .
H9 H 0.545059 0.499921 0.667348 0.101 Uiso 1 1 calc R U . . .
C14 C 0.2748(5) 0.6967(5) 0.2737(3) 0.0876(15) Uani 1 1 d . . . . .
H14A H 0.308824 0.770784 0.283071 0.131 Uiso 1 1 calc R U . . .
H14B H 0.171053 0.684830 0.305931 0.131 Uiso 1 1 calc R U . . .
H14C H 0.255433 0.680231 0.198066 0.131 Uiso 1 1 calc R U . . .
C22 C 1.1437(4) 0.3403(4) 0.2277(3) 0.0756(11) Uani 1 1 d . . . . .
H22A H 1.141988 0.409270 0.262418 0.113 Uiso 1 1 calc R U . . .
H22B H 1.234935 0.338746 0.182572 0.113 Uiso 1 1 calc R U . . .
H22C H 1.162079 0.284810 0.281415 0.113 Uiso 1 1 calc R U . . .
C16 C 0.9105(5) 0.3772(4) -0.0344(3) 0.0719(10) Uani 1 1 d . . . . .
H16 H 0.924901 0.305567 -0.053433 0.086 Uiso 1 1 calc R U . . .
C19 C 0.8619(6) 0.5888(4) 0.0188(5) 0.0913(15) Uani 1 1 d . . . . .
H19 H 0.843476 0.660375 0.036517 0.110 Uiso 1 1 calc R U . . .
C17 C 0.8702(7) 0.4539(6) -0.1137(4) 0.0995(18) Uani 1 1 d . . . . .
H17 H 0.860057 0.433499 -0.185935 0.119 Uiso 1 1 calc R U . . .
C18 C 0.8457(6) 0.5570(5) -0.0881(4) 0.0982(18) Uani 1 1 d . . . . .
H18 H 0.817632 0.607391 -0.142477 0.118 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C3 1.233(3) . ?
O4 C4 1.229(3) . ?
O2 C2 1.231(3) . ?
O5 C5 1.229(3) . ?
N4 H4 0.8600 . ?
N4 C4 1.357(3) . ?
N4 C6 1.392(3) . ?
O6 C6 1.251(3) . ?
N1 H1 0.8600 . ?
N1 C3 1.393(3) . ?
N1 C1 1.357(3) . ?
N5 H5 0.8600 . ?
N5 C4 1.361(3) . ?
N5 C5 1.394(3) . ?
O1 C1 1.230(3) . ?
N3 C3 1.345(3) . ?
N3 C2 1.338(3) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N8 C21 1.482(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.402(3) . ?
N2 C1 1.352(3) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
N7 C13 1.499(4) . ?
N6 C5 1.340(3) . ?
N6 C6 1.333(4) . ?
C7 C13 1.509(4) . ?
C7 C12 1.376(4) . ?
C7 C8 1.372(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.514(5) . ?
C15 C21 1.514(4) . ?
C15 C20 1.372(6) . ?
C15 C16 1.393(5) . ?
C21 H21 0.9800 . ?
C21 C22 1.513(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(4) . ?
C11 C10 1.348(6) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.367(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.397(5) . ?
C9 H9 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.382(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.382(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.338(9) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N4 H4 118.8 . . ?
C4 N4 C6 122.3(2) . . ?
C6 N4 H4 118.8 . . ?
C3 N1 H1 118.4 . . ?
C1 N1 H1 118.4 . . ?
C1 N1 C3 123.1(2) . . ?
C4 N5 H5 117.7 . . ?
C4 N5 C5 124.7(2) . . ?
C5 N5 H5 117.7 . . ?
C2 N3 C3 120.0(2) . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
C21 N8 H8A 109.5 . . ?
C21 N8 H8B 109.5 . . ?
C21 N8 H8C 109.5 . . ?
C2 N2 H2 118.0 . . ?
C1 N2 H2 118.0 . . ?
C1 N2 C2 124.0(2) . . ?
H7A N7 H7B 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
C13 N7 H7A 109.5 . . ?
C13 N7 H7B 109.5 . . ?
C13 N7 H7C 109.5 . . ?
C6 N6 C5 119.4(2) . . ?
O3 C3 N1 117.9(2) . . ?
O3 C3 N3 122.7(2) . . ?
N3 C3 N1 119.5(2) . . ?
O2 C2 N3 124.5(2) . . ?
O2 C2 N2 117.1(2) . . ?
N3 C2 N2 118.4(2) . . ?
O4 C4 N4 123.8(2) . . ?
O4 C4 N5 122.1(2) . . ?
N4 C4 N5 114.0(2) . . ?
O5 C5 N5 117.0(2) . . ?
O5 C5 N6 124.6(2) . . ?
N6 C5 N5 118.3(2) . . ?
O1 C1 N1 122.9(2) . . ?
O1 C1 N2 122.6(2) . . ?
N2 C1 N1 114.4(2) . . ?
C12 C7 C13 122.3(3) . . ?
C8 C7 C13 119.8(3) . . ?
C8 C7 C12 117.8(3) . . ?
O6 C6 N4 117.3(2) . . ?
O6 C6 N6 121.6(2) . . ?
N6 C6 N4 121.1(2) . . ?
N7 C13 C7 110.3(2) . . ?
N7 C13 H13 107.7 . . ?
N7 C13 C14 108.7(3) . . ?
C7 C13 H13 107.7 . . ?
C7 C13 C14 114.5(3) . . ?
C14 C13 H13 107.7 . . ?
C20 C15 C21 122.1(3) . . ?
C20 C15 C16 119.0(3) . . ?
C16 C15 C21 119.0(3) . . ?
N8 C21 C15 111.0(2) . . ?
N8 C21 H21 107.9 . . ?
N8 C21 C22 108.3(3) . . ?
C15 C21 H21 107.9 . . ?
C22 C21 C15 113.8(3) . . ?
C22 C21 H21 107.9 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(4) . . ?
C7 C12 C11 121.6(3) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19 120.2 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(5) . . ?
C18 C17 H17 119.5 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O5 0.86 2.06 2.875(3) 158.7 2_756 yes
N1 H1 O2 0.86 2.04 2.840(3) 154.6 2_645 yes
N5 H5 O1 0.86 2.01 2.859(3) 167.7 1_656 yes
N8 H8A O3 0.89 2.14 2.766(3) 126.4 . yes
N8 H8B O6 0.89 1.95 2.836(3) 176.3 . yes
N8 H8C O4 0.89 2.05 2.871(3) 153.1 2_746 yes
N7 H7A N3 0.89 2.02 2.875(3) 161.6 . yes
N7 H7B O6 0.89 1.95 2.827(3) 169.8 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 O1 -177.5(3) . . . . ?
C3 N1 C1 N2 1.8(4) . . . . ?
C3 N3 C2 O2 -175.4(3) . . . . ?
C3 N3 C2 N2 4.5(4) . . . . ?
C2 N3 C3 O3 -177.6(2) . . . . ?
C2 N3 C3 N1 2.8(4) . . . . ?
C2 N2 C1 N1 6.0(4) . . . . ?
C2 N2 C1 O1 -174.6(3) . . . . ?
C4 N4 C6 O6 179.6(3) . . . . ?
C4 N4 C6 N6 -1.1(4) . . . . ?
C4 N5 C5 O5 176.0(3) . . . . ?
C4 N5 C5 N6 -4.7(4) . . . . ?
C5 N5 C4 O4 -178.8(3) . . . . ?
C5 N5 C4 N4 2.4(4) . . . . ?
C5 N6 C6 N4 -1.2(4) . . . . ?
C5 N6 C6 O6 178.1(3) . . . . ?
C1 N1 C3 O3 174.1(2) . . . . ?
C1 N1 C3 N3 -6.4(4) . . . . ?
C1 N2 C2 O2 170.5(3) . . . . ?
C1 N2 C2 N3 -9.5(4) . . . . ?
C7 C8 C9 C10 1.4(7) . . . . ?
C6 N4 C4 O4 -178.2(3) . . . . ?
C6 N4 C4 N5 0.5(4) . . . . ?
C6 N6 C5 O5 -177.0(3) . . . . ?
C6 N6 C5 N5 3.8(4) . . . . ?
C13 C7 C12 C11 -179.5(3) . . . . ?
C13 C7 C8 C9 178.8(4) . . . . ?
C15 C20 C19 C18 -1.5(6) . . . . ?
C15 C16 C17 C18 -1.3(7) . . . . ?
C21 C15 C20 C19 -178.8(3) . . . . ?
C21 C15 C16 C17 -179.8(3) . . . . ?
C11 C10 C9 C8 0.0(6) . . . . ?
C12 C7 C13 N7 84.3(4) . . . . ?
C12 C7 C13 C14 -38.7(5) . . . . ?
C12 C7 C8 C9 -2.0(6) . . . . ?
C12 C11 C10 C9 -0.7(6) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C8 C7 C13 N7 -96.6(4) . . . . ?
C8 C7 C13 C14 140.5(4) . . . . ?
C8 C7 C12 C11 1.3(5) . . . . ?
C20 C15 C21 N8 60.3(4) . . . . ?
C20 C15 C21 C22 -62.1(4) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
C20 C19 C18 C17 0.8(7) . . . . ?
C16 C15 C21 N8 -119.3(3) . . . . ?
C16 C15 C21 C22 118.3(4) . . . . ?
C16 C15 C20 C19 0.8(5) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.648
